Look Closely Before Leaping From a Steady but Unfulfilling Job

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DeJuan Stroud, a former Wall Street broker and compliance officer, said he had an existential crisis 20 years ago. After more than a decade working on Wall Street, he was miserable, so he took the risk of turning a hobby into a business.CreditEmily Goodnight

WITH bonus checks now sitting in bank accounts and the malaise of winter settling in over the holiday weekend, some people may be dreaming of leaving their career to follow a latent passion.

For a dose of reality, though, consider the tale of DeJuan Stroud, a former Wall Street broker and compliance officer.

Mr. Stroud said he had a true existential crisis sitting in a car late one night 20 years ago. After more than a decade working on Wall Street, he was miserable.

“Everything was negative,” he said. “A lawsuit. Brokers complaining. Clients losing money. It was that constant negative. It just began to wear you down. I couldn’t imagine feeling fulfilled.”

But he had four children and a wife who stayed home to care for them.

“My wife and I sat down and said, ‘Can we? Should we?’” Mr. Stroud said.

They decided they could, and he gave up his well-paid job and put their modest savings at risk to turn a hobby — floral design, which he had learned from his grandmother growing up in Alabama — into a business.

Now, two decades later, Mr. Stroud is one of the most sought-after floral and event designers in New York City.

His is a success story. But there are big risks in following a similar path — giving up a regular salary and losing your savings for one; throwing away the security of a career is another. For those who go forward, the payoff may be more psychic than monetary, and they need to feel comfortable that the chance of a more modest lifestyle is worth it.

“We have this myth that is still following us that you prepared for one career, you got a job in it and you stayed there for 30 years,” said Helen Harkness, founder of Career Design Associates, near Dallas. “We’re still dealing with that with midcareer people even though most know it’s a dead myth.”

Myth or not, trading a well-paying, secure career for the chance to try something different is not an option for a lot of people, particularly for those who do not have wealth, or at least a hefty bank account, as a backstop.

“We financed the business with some savings we had and a small-business loan guaranteed by our home,” Mr. Stroud said. “It was kind of scary. But when you reach that point of, ‘I can’t do this another day,’ you choose that fear over that misery.”

Still, a Gallup Poll in October found that when American workers make a career change, they almost always do so by leaving their employer instead of taking a new job within the company. Some 93 percent said they took a new role elsewhere. The survey found this was true whether the job change occurred 30 years ago or within the last year.

While most people take similar jobs at other companies, Dr. Harkness said, the executives who work with her firm have realized that jumping to another company will not satisfy them.

“The people who come to me who have the easiest time are people who recognize this is an opportunity for them to gain what they didn’t have before,” she said. “They’re accepting the fact that life will be better after this. It’s their expectation. They don’t doubt it, even though this is not an easy process.”

Those who stay put, Dr. Harkness said, may not realize the opportunity. But some are perfectionists, she said, paralyzed by trying to get everything right before moving.

“When you’re changing careers, you can’t be a perfectionist,” she said. “You have to get insight and counseling and then you have to take some risks. You have to identify that risk and be prepared to deal with it. Some people who have been very careful, they can’t turn loose of that.”

Robert Cox, a former bond salesman, is on his second big switch. When he turned 40, in 2000, he left Wall Street to go into real estate in the Hamptons, the wealthy summer haven on Long Island. He and his wife bought and renovated homes. But in 2012, they divorced, and he began looking for another career change.

He had been a vegan since 2000, and he said he struggled to find good, quick vegan food when he moved back to Manhattan. That gave him the idea for a fast vegan chain, VBurger, which opened its first restaurant in Manhattan last fall.

Mr. Cox said his newest career was driven as much by a humanitarian aspect of not eating animals as it was about serving what he sees as an untapped niche in the fast-food world.

“I am mindful of the fact that restaurants don’t always work out,” he said. “It’s good to have some sort of backup plan. I do have some reserves that I can fall back on, but I would breathe a lot more easily if it was profitable at a certain amount of time.”

Fear of financial failure keeps many people from taking these risks.

Mr. Stroud, who recently designed a wedding in Hawaii where the ceremony moved through a series of tents created to evoke the homes the couple owned or loved in Las Vegas, Paris, London and Hong Kong, said it wasn’t clear for at least the first seven years that he was going to keep his business afloat. And he counsels others thinking of making a similar switch to be sure they understand the risks.

“Career and financially, are you really at that place where you’re that unhappy with what you’re doing that the remembrance of that unhappiness keeps you pushing ahead?” he said. “In 13 years on Wall Street, I interviewed with other firms and thought I’d go somewhere else. But it was still the same unfulfilling day-to-day job.”

That was how Kathy Andersen felt 16 years ago. She had risen quickly within Ford Motor in Australia and was earning a six-figure salary and living in a nice apartment in Sydney.

“I realized I was really suffering and not happy and I needed to make a change,” she said.

She sold most of her possessions and had enough money for six months of travel.

In Miami, near the end of her trip, she heard about a nonprofit organization that helped children by teaching them sailing. She sailed, so she volunteered. That led to work in Haiti and eventually to the John F. Kennedy School of Government at Harvard for graduate school.

“I needed to see life differently,” she said. “I saw it like a chessboard. If I made this move, I’d get here. It gave me a sense of security. I was a planner.”

“When I stopped, when I saw life as a piece of art that takes shape with each step we take, something happens that we can never plan for,” she added.

After years of working at various nonprofit groups, Ms. Andersen is now a life coach in South Florida where she helps people leave their jobs — or at least find something they can enjoy in their present career.

“People say, ‘How could you leave your job? I could never do that,’” she said. “My work with people is to say, ‘Start where you are and write down the things you want. It gets you to the things you need. Then it gets to what one thing could you do today.’ ”

These are people for whom a second or third career has paid off — and who had the luxury of trading one highly paid job for another. That’s not always the case.

And even Mr. Stroud, who said he now earned far more than he ever did on Wall Street, struck a cautious note.

“My wife and I say all the time, ‘Thank goodness we didn’t know what we didn’t know,’” he said. “It was truly such a jump.”

Correction:

An earlier version of this article misspelled the surname of a woman who left her job at Ford Motor in Australia to change careers. She is Kathy Andersen, not Anderson.

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A version of this article appears in print on , on Page B4 of the New York edition with the headline: How to Decide When It’s Time to Jump Ship. Order Reprints | Today’s Paper | Subscribe